A lot of situations come to a head on this episode of The Carrie Diaries titled, A first Time for Everything. Carrie, Dorrit, their dad and Mouse all find themselves in new emotional situations. This begins with Carrie and Sebastian playing a board game together. Sebastian looks at Carrie and says, “I love you Carrie Bradshaw” and Carrie, stunned, blurts out the wrong thing and says “I want to have sex with you.” Sebastian seems to like what Carrie says, but now Carrie feels pressured to tell Sebastian she loves him; she loves so much it hurts her. Carrie cannot figure out why she said she said one thing when she meant another.
Madonna has just released her Like a Virgin album, and Interview Magazine is hosting the launch party at the Oak Room Plaza. Carrie thinks bringing Sebastian will make it the perfect night to tell him she loves him: The can rent a hotel room, where Carrie will make her sexual debut. When Carrie works herself up to finally tell Sebastian she loves him, they’re on the train on the way to the party. The train conductor asks them for their tickets, ruining her moment.
Meanwhile, Tom’s new girlfriend, Donna, invites him over for a “night cap” and Dorrit goes to visit Miller from the record store. He tells her that if she doesn’t want to stand out, she shouldn’t’ wear thick and Goth-like makeup but look like everyone else to blend in. They also talk about books, and Miller gives her one that has a lot to do with sex. Ironically, Donna gives Dorrit the best and worst advice when she tells her not to confuse sex with love, and that sex is like a transaction. Eventually, Dorrit, who is 15, takes Miller home to make her sexual debut.
Carrie on the other hand, is making a mess of things with Sebastian at the VIP party. Only Carrie has a VIP bracelet, so she leaves him to help Bennett get a quote from the guy who wrote Like a Virgin for Madonna. She keeps telling Sebastian how sorry she is that she left him alone, but Sebastian yells that he can handle being on his own and doesn’t need her to take care of him.
Carrie and Sebastian get into a big fight, as Sebastian claims that the party was all about Carrie getting her by-line (“new love makes you feel like you`ve been touched for the very first time”). Carrie accuses Sebastian of putting up walls, and he accuses of her of not being honest about her feelings. Carrie`s big mouth ends up doing something else she does not want to do: Break up with Sebastian.
Tom also makes a mistake when he criticizes Debbie for sleeping with him when she had her little boy home. Tom runs into him naked while trying to find the bathroom. They make up at the diner at the end of the episode and decide that fighting is normal when you are dating. Debbie promises to get a babysitter for her little boy next time.
Wes is really into Mouse, who although Mouse likes Wes, she will not admit to it. The reason is because of her old boyfriend, Seth. Mouse became so focused on Seth that her grades slipped and Wes became number one in the class because she was so into having sex with him all the time. She thinks Wes will be a distraction, but it turns out the principal promises to write them both letters for university after Wes hands in minutes from Mouse`s Astronomy Club meeting. Mouse decides that to become number one she must join all the clubs to beat Wes into Harvard.
As for Carrie, she is in so much pain from breaking up with Sebastian she cannot even write in her journal at the end of the night. All Carrie needs to do is admit her feelings to Sebastian, but she can’t figure out why it’s so hard for the words to come out right in person or on paper.